N-Heterocyclic carbene copper-catalyzed direct alkylation of terminal alkynes with non-activated alkyl triflates

Liqun Jin; Wangfang Hao; Jianeng Xu; Nan Sun; Baoxiang Hu; Zhenlu Shen; Weimin Mo; Xinquan Hu

doi:10.1039/c7cc00891k

N-Heterocyclic carbene copper-catalyzed direct alkylation of terminal alkynes with non-activated alkyl triflates

Chem Commun (Camb). 2017 Apr 6;53(29):4124-4127. doi: 10.1039/c7cc00891k.

Authors

Liqun Jin¹, Wangfang Hao², Jianeng Xu², Nan Sun², Baoxiang Hu², Zhenlu Shen², Weimin Mo², Xinquan Hu¹

Affiliations

¹ College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, P. R. China. liqunjin@zjut.edu.cn xinquan@zjut.edu.cn and State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, the Chinese Academy of Sciences, Lanzhou 730000, P. R. China.
² College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, P. R. China. liqunjin@zjut.edu.cn xinquan@zjut.edu.cn.

PMID: 28352858
DOI: 10.1039/c7cc00891k

Abstract

(NHC)-Cu-catalyzed C(sp)-C(sp³) bond formation has been successfully achieved under mild conditions. Nonactivated alkyl triflates, which could be easily derived from alcohols, were utilized as C-O electrophiles. Mechanistic studies suggested that copper acetylide was the active species. Scale-up reactions further demonstrated the practicality and efficiency of the developed strategy.